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Synthese von 4-Benzylthio- und 4-(Arylthio)-1,3-oxazol-5(2H)-onen


Wipf, Peter; Prewo, Roland; Bieri, Jost H; Heimgartner, Heinz; Nastopoulos, Vassilios; Germain, Gabriel (1987). Synthese von 4-Benzylthio- und 4-(Arylthio)-1,3-oxazol-5(2H)-onen. Helvetica Chimica Acta, 70:1380-1388.

Abstract

Following a known procedure, 4-(benzylthio)-1,3-oxazol-5(2H)-one (4a) was synthesized starting from sodium cyanodithioformate (1) and cyclohexanone (Scheme 1). The structure of the intermediate4-(benzylthio)-1,3-thiazol-5(2H)-one (3a) was established by X-ray crystallography. An alternative route was developed for the synthesisof 4-(arylthio)-1,3-oxazol-5(2H)-ones which are not accessible by the former reaction. Treatment of ethyl cyanoformate (5) with a thiophenol in the presence of catalytic amounts of Et3NH andTiCI4, followed by addition of a ketone and BF3.Et2O in a one-pot-reaction, gave 4f-i in low-to-fair yields (Scheme 3). Both synthetic pathways -complementary as for benzyl-S and aryl-S derivatives - seem to be limited with respect to variation of substituents of the ketone.

Abstract

Following a known procedure, 4-(benzylthio)-1,3-oxazol-5(2H)-one (4a) was synthesized starting from sodium cyanodithioformate (1) and cyclohexanone (Scheme 1). The structure of the intermediate4-(benzylthio)-1,3-thiazol-5(2H)-one (3a) was established by X-ray crystallography. An alternative route was developed for the synthesisof 4-(arylthio)-1,3-oxazol-5(2H)-ones which are not accessible by the former reaction. Treatment of ethyl cyanoformate (5) with a thiophenol in the presence of catalytic amounts of Et3NH andTiCI4, followed by addition of a ketone and BF3.Et2O in a one-pot-reaction, gave 4f-i in low-to-fair yields (Scheme 3). Both synthetic pathways -complementary as for benzyl-S and aryl-S derivatives - seem to be limited with respect to variation of substituents of the ketone.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1987
Deposited On:21 May 2014 14:38
Last Modified:05 Apr 2016 17:52
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel

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